Radical coupling reactions of piceatannol and monolignols: A density functional theory study

Elder T.; Río Andrade, José Carlos del; Ralph, John; Rencoret, Jorge; Kim, Hoon; Beckham, Gregg T.; Agencia Estatal de Investigación (España)

Radical coupling reactions of piceatannol and monolignols: A density functional theory study

12 páginas.- 13 figuras.- 1 tabla.- 41 referencias.- Supporting information: Cartesian coordinates for low energy conformation of all compounds, optimized using M06-2X/6-311++G(d,p).

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Main Authors:	Elder T., Río Andrade, José Carlos del, Ralph, John, Rencoret, Jorge, Kim, Hoon, Beckham, Gregg T.
Other Authors:	Agencia Estatal de Investigación (España)
Format:	artículo biblioteca
Language:	English
Published:	Elsevier 2019-08
Subjects:	Coniferyl alcohol, Density functional theory (DFT), P-coumaryl alcohol, Piceatannol, Quinone methide, Sinapyl alcohol, Stilbene,
Online Access:	http://hdl.handle.net/10261/181779 http://dx.doi.org/10.13039/501100010198 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 http://dx.doi.org/10.13039/100000001 http://dx.doi.org/10.13039/501100011033
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spelling	dig-irnas-es-10261-1817792020-08-27T17:55:58Z Radical coupling reactions of piceatannol and monolignols: A density functional theory study Elder T. Río Andrade, José Carlos del Ralph, John Rencoret, Jorge Kim, Hoon Beckham, Gregg T. Agencia Estatal de Investigación (España) Ministerio de Economía y Competitividad (España) Ministerio de Economía, Industria y Competitividad (España) European Commission National Science Foundation (US) Río Andrade, José Carlos del [0000-0002-3040-6787] Ralph, John [0000-0002-6093-4521] Rencoret, Jorge [0000-0003-2728-7331] Kim, Hoon [0000-0001-7425-7464] Elder T. [0000-0003-3909-2152] Beckham, Gregg T. [0000-0002-3480-212X] Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene 12 páginas.- 13 figuras.- 1 tabla.- 41 referencias.- Supporting information: Cartesian coordinates for low energy conformation of all compounds, optimized using M06-2X/6-311++G(d,p). Recent experimental work has revealed that the hydroxystilbene piceatannol can function as a monomeric unit in the lignification of palm fruit endocarp tissues. Results indicated that piceatannol homo-couples and cross-couples with monolignols through radical reactions and is integrally incorporated into the lignin polymer. The current work reports on the thermodynamics of the proposed reactions using density functional theory calculations. The results indicated that, in general, the energetics of both homo-coupling and cross-coupling are not dissimilar from those of the monolignol coupling, demonstrating the compatibility of piceatannol with the lignification process. Moreover, the DFT methods appear to predict the correct courses of post-coupling rearomatization reactions. © 2019 This work used the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by National Science Foundation grant number ACI-1548562 . Specifically, it used the Bridges system at the Pittsburgh Supercomputing Center (PSC) and Stampede2 at the Texas Advanced Computing Center ( TACC ), both via MCB-090159 to GTB. JR and HK Were funded by the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494 and DE-SC0018409 ). JRe and JCdR were funded by the Spanish Projects CTQ2014-60764-JIN and AGL2017-83036-R (financed by Agencia Estatal de Investigación, AEI and Fondo Europeo de Desarrollo Regional, FEDER). GTB acknowledges support from the US Department of Energy Office of Energy Efficiency and Renewable Energy Bioenergy Technologies Office under Contract No. DE-AC36-08GO28308 to the National Renewable Energy Laboratory. Peer reviewed 2019-05-20T11:44:47Z 2019-05-20T11:44:47Z 2019-08 artículo http://purl.org/coar/resource_type/c_6501 Phytochemistry 164: 12-23 (2019) 0031-9422 http://hdl.handle.net/10261/181779 10.1016/j.phytochem.2019.04.003 http://dx.doi.org/10.13039/501100010198 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 http://dx.doi.org/10.13039/100000001 http://dx.doi.org/10.13039/501100011033 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-60764-JIN AGL2017-83036-R/AEI/10.13039/501100011033 info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/AGL2017-83036-R http://dx.doi.org/10.1016/j.phytochem.2019.04.003 Sí none Elsevier
institution	IRNAS ES
collection	DSpace
country	España
countrycode	ES
component	Bibliográfico
access	En linea
databasecode	dig-irnas-es
tag	biblioteca
region	Europa del Sur
libraryname	Biblioteca del IRNAS España
language	English
topic	Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene
spellingShingle	Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene Elder T. Río Andrade, José Carlos del Ralph, John Rencoret, Jorge Kim, Hoon Beckham, Gregg T. Radical coupling reactions of piceatannol and monolignols: A density functional theory study
description	12 páginas.- 13 figuras.- 1 tabla.- 41 referencias.- Supporting information: Cartesian coordinates for low energy conformation of all compounds, optimized using M06-2X/6-311++G(d,p).
author2	Agencia Estatal de Investigación (España)
author_facet	Agencia Estatal de Investigación (España) Elder T. Río Andrade, José Carlos del Ralph, John Rencoret, Jorge Kim, Hoon Beckham, Gregg T.
format	artículo
topic_facet	Coniferyl alcohol Density functional theory (DFT) P-coumaryl alcohol Piceatannol Quinone methide Sinapyl alcohol Stilbene
author	Elder T. Río Andrade, José Carlos del Ralph, John Rencoret, Jorge Kim, Hoon Beckham, Gregg T.
author_sort	Elder T.
title	Radical coupling reactions of piceatannol and monolignols: A density functional theory study
title_short	Radical coupling reactions of piceatannol and monolignols: A density functional theory study
title_full	Radical coupling reactions of piceatannol and monolignols: A density functional theory study
title_fullStr	Radical coupling reactions of piceatannol and monolignols: A density functional theory study
title_full_unstemmed	Radical coupling reactions of piceatannol and monolignols: A density functional theory study
title_sort	radical coupling reactions of piceatannol and monolignols: a density functional theory study
publisher	Elsevier
publishDate	2019-08
url	http://hdl.handle.net/10261/181779 http://dx.doi.org/10.13039/501100010198 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 http://dx.doi.org/10.13039/100000001 http://dx.doi.org/10.13039/501100011033
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_version_	1777665018952679424

Radical coupling reactions of piceatannol and monolignols: A density functional theory study

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